Sicily and Its Isles

Sicily and Its Isles

May 14th-28th, 2026

Small Group Tour (Maximum 24 people)

 

Days 1 | Thursday, May 14, 2026 | Overnight Flight: You're on your way to Sicily - an island paradise nestled amongst the deep blue waves of the Mediterranean. Look past the Italy you think you know and see how this coastal farmland balances ancient traditions and modern comforts.

 

Day 2 | Friday, May 15, 2026 | Palermo: Arrive in Palermo (UNESCO), Sicily's welcoming capital city. Uncover the island's deeply rooted heritage, teeming with Arab-Norman architectural masterpieces and delicate Classical designs. Come to know your fellow travelers over a welcome dinner. (Hotel Porta Felice) D

 

Day 3 | Saturday, May 16, 2026 | Palermo: Begin your adventure tasting your way through Palermo’s lively markets on a walking tour unveiling the city's historical center and introducing you to traditional Sicilian street food. Palermo's culinary heritage layers Arab and Norman influences with local produce such as wild fennel, olives, and spices. This afternoon, head to Monreale Cathedral, ascending on foot to see its majestic Byzantine mosaics. Then, it's your choice! Explore the cathedral’s cloisters, taking in their serene atmosphere of the monastic complex or ascend the southern tower to the panoramic terraces for a bird’s-eye view over Palermo. (Hotel Porta Felice) B, L

 

 

Day 4 | Sunday, May 17, 2026 | Palermo - Marsala | Make your way to Alcamo, a hilltop town deeply nestled in Sicily's largest wine-producing region. Venture off the beaten path and meet a local winemaker. Learn about the local types of grapes and production techniques, before joining a hands-on cooking class. Share the meal you prepared for lunch, paired with the farm's own wines. Late this afternoon, settle into your hotel in coastal Marsala for a three-night stay. Perhaps you'll take a sunset walk along the waterfront before heading out for an evening at leisure. (Grand Hotel Palace) B, L

 

Day 5 | Monday, May 18, 2026 | Marsala: Discover the ancient craft of sea-salt harvesting during a guided visit to the salt pans of the Stagnone Lagoon, once at the confluence of Phoenician, Greek, and Roman civilizations. Hop on a local boat and take in the views of the lagoon and surrounding, low-lying islands before returning to Marsala for an afternoon at leisure. (Grand Hotel Palace) B

 

Day 6 | Tuesday, May 19, 2026 | Marsala: The day is yours to explore Marsala as you please. Perhaps you'll visit one of the city's numerous wineries, noted for producing the eponymous fortified wine. Or, you may join a full day optional excursion to Favignana. A short waterjet ride from Sicily's mainland, Favignana island is part of the Egadi archipelago. Once famous for its tuna fish production, this small island boasts crystal clear waters and enchanting gardens. (Grand Hotel Palace) B

 

 

Day 7 | Wednesday, May 20, 2026 | Marsala - Agrigento: This morning, experience an Impact Moment when you visit an olive oil maker who uses ethical farming methods to produce EVOO. Hear this local man's story, his dedication to sustainable farming, and how he stands up against the rules that the mafia tries to impose on local farmers. Explore the olive groves on foot and pause for a rustic picnic-style lunch before continuing to Agrigento's seaside. Settle in for a one-night stay and dinner at your hotel. (Baia di Ulisse) B, L, D

 

Day 8 | Thursday, May 21, 2026 | Argigento - Cefalú Coast: In company of an expert guide, wander through the imposing Greek ruins of Agrigento's Valley of the Temples (UNESCO). Discover the myths enshrouding the fountain of ancient Akragas, and watch history come alive. Then, relax aboard your motorcoach during a full afternoon transfer to Sicily's northern coast. As the sun sets, acquaint yourself with the extensive grounds of your cliffside resort. (Mangia's Pollina Resort) B, D

 

Day 9 | Friday, May 22, 2026 | Cefalú Coast: Today, set off for the seaside town of Cefalú on Sicily's northern coast. Stroll the medieval streets and enjoy ample free time to explore on your own. Perhaps you'll peek into the city's impressive cathedral showcasing Norman architecture, or take in Sicilian medieval art at the Mandralisca museum. Return to your coastal resort mid-afternoon. You will have time to venture down to the resort's private beach and dip your feet in the Mediterranean, if you choose. (Mangia's Pollina Resort) B, D

 

Day 10 | Saturday, May 23, 2026 | Cefalú Coast - Ferry to Aeolian Islands - Isle of Salina: Grab your bags and hop on a ferry in Milazzo. Sail by Vulcano and Lipari on your way to Salina, a far-flung isle surrounded by vibrant blue waters and dark volcanic rock. Somewhat off the beaten path, Salina is one of the less-traveled Aeolian Islands, preserved as a vacation getaway for Italians. Start your 2-night stay and slow your rhythm to the gentle pace of this small island. (Hotel La Salina Borgo Di Mare) B

 

Day 11 | Sunday, May 24, 2026 | Salina: Dramatic landscapes of rocky cliffs and vibrant vineyards pass you by on your way to nearby Pollara, famous for its traditional caper cultivation. Wander through the fields, tasting the salted flower buds accompanied by a glass of Malvasia, a locally produced dessert wine. The afternoon is yours to do as you please. Perhaps you'll find a café by the sea and soak in the local life while sampling their every flavor of granita ice-slush. (Hotel La Salina Borgo Di Mare) B

 

Day 12 | Monday, May 25, 2026 | Salina - Ferry to Sicily - Taormina: Early this morning, ferry back to mainland Sicilia. Journey along the Ionian Coast to Taormina, a seaside hub of ancient Greek theaters and hilly walkways. Discover its well-preserved Greek theatre in company of a local guide. Walk in the footsteps of ancient attendees and take in an unparalleled viewpoint of the adjacent sea. Spend the evening on your own. Perhaps you'll grab a bite to eat at a sidewalk café, or peruse the local boutiques for handcrafted souvenirs. (Excelsior Palace Hotel Taormina) B

 

 

Day 13 | Tuesday, May 26, 2026 | Taormina - Mount Etna - Taormina: See Sicily's wilder side on an off-road adventure to Mount Etna. Stare up at the iconic peak as your vehicle climbs along the sides of Europe's largest active volcano. Spend the day exploring this legendary giant, passing by lava formations and basalt rocks. This evening, toast to your Sicilian sojourn at dinner, surrounded by local musicians. (Excelsior Palace Hotel Taormina) B, D

 

Day 14 | Wednesday, May 27, 2026 | Taormina - Tour Ends: Your journey through Sicily comes to a close today. Return home with memories of Italy's favorite island. B

 

Luggage fees NOT included in price of trip

 

 

Timi's Tours offers Travel Protection through Trip Mate. The Pre-Existing Medical Condition Exclusion Waiver is available if Travel Protection is purchased at the same time you make your Timi's Tours deposit (or within 15 days). For questions about coverage please call our office.

Travel Insurance price per person:

Single: $811.35

Double: $721.15

 

Activity Level: 4

*Our Activity levels are a 1-4 scale. To view what each level includes, please go to the  “Policy” tab on the website*